New anthraquinone dye and dyeing therewith



Patented Julie 3, 1930 v UNITED STATES ARNOLD SHEPHERDSON AND WILLIAM WYNDHAM TATUM, OF MANCHESTER, ENG- LAND, ASSIGNORS TO BRITISH DYESTUFFS CORPORATION LIMITED, HAN-- CHESTER, ENGLAND NEW AN THRAQUIN ONE DYE AND DYEING THEREWITH 1T0 Drawing. Application filed January 27, 1928, Serial No. 250,094, and in Great Britain August 19, 1926.

' Renewed October 21, 1929;

The production of dyes by the action of sulphites upon halogen-amino-hydroxyanthraquinones of the general formula:

0 orr NHR I where R is an aryl group and H1 is a halogen has heretofore been proposed. In one way of hydroxy-2-chlor-4-tolylamino-anthraquinone (such as may be obtained, for example, by

heating 1-hydroXy-2 4-dichlor-anthraquinone with p-toluidine) are dissolved in 700 parts of phenol in an autoclave and treated with a solution of 180 parts of sodium sulphite cryse tals in 470 parts of water. The autoclave is then scaled up and the whole heated at a tem-- perature of 150 to 180 C(for 5 hours. The phenol is steamed off and the new dyestufl' isolated from the filtered liquor by adding salt.

'25 The new product forms, when dry, a blue powder soluble in water with a reddish-blue colour. From an acidulated dyebath, wool is dyed in brilliant reddish-blue shades of excellent fastness properties We have now further found that valuable acid dyes are obtained by a similar process from sulphonated derivatives of the above type in which the aryl radical R carries a sulphonic group. Such sulphonated derivatives may be prepared from 2.4-dichlor0 or 2.4-

dibromo-erythrohydroxyanthraquinone by reaction with an arylamine, followed by sulphonation, as described "in British specifi- 0 cation No. 21,897 of 1900. The disulphonated products obtained according to our invention by the substitution of the betahalogen atom by a sulphonic group differ from the'monosulphonated products already as known in possessing greatly increased soluinvention relates. The present application is concerned with the anilino derivatives and is a continuation in part of the above co-pending application.

One method of carrying out our invention is as follows, the parts bemg by-weight: making dyes in this way 100 parts of 1-- Emample 100 parts of the sodium salt of 2-chloro-1- hydroxy 4 (p-sulphoanilino) anthraquinone of the structure- SOsNB anilinoanthraquinone of M. P. 194.195 C.)

are boiledwith a solution of 100 parts of sodium sulphite crystals in 4000 parts of water until a test sample is practically completely soluble when cold. Any traces of unchanged mono-sulphonate are then filtered ofi cold, and the disulphonate is isolated by evaporati n of the filtrate.

The dyestufi is then obtained in the form of its sodium salt. The free acids possess no advantage over the salts obtained in this way.

100 parts of wool are introduced into a bath containing 1 part of the-colouring matter'so isolated, 10 parts of Glaubers salt, 4 parts of sulphuric acid and 5000 parts of water. On raising the temperature, the colour is rapidly absorbed by the wool, which after an hours boiling becomes dyed a reddish-blue shade of excellent fastness. After-chroming turns the'shade green.

When it is desired to produce the dyestufi in the form of free acid, the liquors obtained by filtering off the mono-sulphate may be acidified before evaporation.

What we claim and desire to secure by Letters Patent is 1. The manufacture of new acid dyestufis of the general type: a

CO (I 0.11 oo I NB-B.SOIH

where R represents a divalent aryl residue, in the form of a sodium salt, consisting in treating a sodium salt of a 2-chlbro-l-hydroxy-4-sulphoanilinoanthraquinone with a solution of a metal sulphite, removing unchanged monosulphonate by filtration in the cold, and evaporating the filtrate. v

2; The acid d estufi, being a 2-sulphonic derivative of 4- (111 h0nanilino)-1-hydroxyanthraquinone, and aving in the form of its sodium salt the formula no Odie go en -BO|Na in substance and on the animal fibre, the said dyestufi'being a dark violet powder, soluble in water and in dilute acids to purple solutlons, and m concentrated sulphuric acid to a green solution "becoming blue on addition of boric acid, giving when dyed on wool or silk from an ac1d bath, redder shades than the corzfspondmg 4-(sulpho-p-toluidino) derivav In testimony whereof we aflix our signatures,

ARNOLD SHEPHERDSON. WILLIAM WYNDHAM TATUM. 

